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Methanol → p-Toluenesulfonic acid

HRID 259719
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HRID 259719 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:18]([O:20][CH3:21])=[O:19])[C:8](=[CH:13][C:14]=1[N+:15]([O-])=O)[C:9]([O:11][CH3:12])=[O:10])(=O)[CH3:2].CO.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([OH:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1>[Pt].C1(C)C=CC=CC=1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([OH:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.[CH3:2][C:1]1[NH:15][C:14]2[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([C:18]([O:20][CH3:21])=[O:19])=[CH:6][C:5]=2[N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 14574474Dimethyl 4-acetamido-5-nitrophthalate

생성물 2

HCID 6101p-Toluenesulfonic acidHCID 21827571HCID 21827571, 화합물

시약·촉매·용매 2

HCID 23939Platinum촉매
HCID 1140
Toluene
용매

실험 절차

A mixture of dimethyl 4-acetamido-5-nitrophthalate, methanol and 5% platinum on carbon is hydrogenated in a Parr hydrogenator. The reaction mixture is filtered through diatomaceous earth and the filtrate is concentrated in vacuo. The thus-obtained crude diamine intermediate (48.09, 0.180 mol) is mixed with p-toluenesulfonic acid (51.4 g, 0.270 mol) and toluene (400 mL), and stirred for 2 hours at reflux temperatures with azeotropic removal of water, cooled and concentrated in vacuo. The resultant residue is recrystallized from methanol to afford the p-toluene sulfonate salt of the title product. The salt is dissolved in hot water, made basic with sodium bicarbonate and extracted with methylene chloride. The combined extracts are washed with brine, dried (MgSO4) and concentrated in vacuo to give a red solid. Recrystallization of a portion of the red solid affords the title product as white crystals, mp 151°-152° C.

후처리

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe thus-obtained crude diamine intermediate (48.09, 0.180 mol)
  4. temperatureat reflux temperatures
  5. customwith azeotropic removal of water
  6. temperaturecooled
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is recrystallized from methanol

출처 및 근거

ORD 기록
ord-03bc7dc89f474844b6f732b87341517e
출처 데이터셋
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05523279

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